Carbon Dioxide → 5-[(3,7,11,15-Tetramethylhexadecyl)oxy]thiophene-2-carboxylic acid

HRID 596659노트

반응식

HRID 596659 반응식
[CH3:1][CH:2]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:3][CH2:4][O:5][C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[C:27](=[O:29])=[O:28].C(O)C.O>CCOCC.[Na].[Hg]>[CH3:1][CH:2]([CH2:11][CH2:12][CH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:3][CH2:4][O:5][C:6]1[S:7][C:8]([C:27]([OH:29])=[O:28])=[CH:9][CH:10]=1

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 702EthanolHCID 962WaterHCID 214418222-[(3,7,11,15-Tetramethylhexadecyl)oxy]thiophene

생성물 1

HCID 214418155-[(3,7,11,15-Tetramethylhexadecyl)oxy]thiophene-2-carboxylic acid

시약·촉매·용매 2

HCID 9837419Sodium amalgam촉매HCID 3283Diethyl Ether용매2회

실험 절차

When in Example 3, 1-bromo-3,7,11,15-tetramethylhexadecane is substituted for 1-bromohexadecane, 2-(3,7,11,15-tetramethylhexadecyloxy)thiophene is obtained. A solution of 38.1 g (0.1 mole) of 2-(3,7,11,15-tetramethylhexadecyloxy)-thiophene in 50 ml of anhydrous ether is added over a 4 hour period to 6.0 g of sodium amalgam in 100 ml of hydrous ether at reflux temperature (36°-39° C) under slight nitrogen pressure. The mixture is refluxed an additional 2 hours, then cooled to room temperature and carbonated by adding freshly crushed dry ice after which 20 ml of ethanol is added dropwise followed by the addition of 50 ml of water. The aqueous solution is separated from the ether layer, filtered and acidified with hydrochloric acid to precipitate 5-(3,7,11,15-tetramethylhexadecyloxy)-2-thiophenecarboxylic acid.

후처리

  1. temperatureat reflux temperature (36°-39° C) under slight nitrogen pressure
  2. temperatureThe mixture is refluxed an additional 2 hours
  3. additionis added dropwise
  4. customThe aqueous solution is separated from the ether layer
  5. filtrationfiltered
  6. customto precipitate 5-(3,7,11,15-tetramethylhexadecyloxy)-2-thiophenecarboxylic acid

출처 및 근거

ORD 기록
ord-efcf802ecf4c4103a9c5a40594377451
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04011333

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